


Faux Pas and Fumbles (Love You Anyways)

by xKookiesandCreamx



Category: Teen Wolf (TV)
Genre: Alternate Universe - High School, Attempting to make the boypussy thing less strange, Basically Stiles and Derek figuring out how to do the do with some fluff thrown in, Boypussy Stiles Stilinski, But is still Male, Childhood Friends, First Time, Friends to Lovers, Give it a shot I promise its not as weird as it sounds, Growing Up Together, He's not transgender, JUST, M/M, Magical stiles, Multi, Sexual Slip Ups, Sheriff Stilinski's name is John kiss my ass Jeff Davis, Spark Stiles, Stiles Has a Vagina, Virgin Derek, Virgin Stiles Stilinski
Language: English
Status: Completed
Published: 2017-01-03
Updated: 2017-01-03
Packaged: 2018-09-13 12:10:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 19,444
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9123019
Author URL: https://archiveofourown.org/users/xKookiesandCreamx/pseuds/xKookiesandCreamx
Summary: But, even if Derek grew some balls and finally made a move, and him and Stiles actually got together, Derek wouldn't be fucking Stiles up the ass.He means he could if Stiles really wanted him to, but Derek doubts it would be all that pleasurable for him.Because Stiles might be a boy from the torso up.But downwards he's female.**Also known as the friends to lovers high school au that features Stiles magically having female reproductive organs due to Spark Magic, yet still being a guy





	

"Der wake up! Wake up! It's time for your game! Come onnnn!" Derek winced at Stiles's excited yelling in his ear.

He sat up with a grunt, chuckling when his change in position caused his human alarm clock to fall off him and the bed, landing on the carpet in a gangly heap.

Said human alarm clock was none-other-than Stiles Stilinski.

 

Stiles Stilinski, aka Derek's best friend since they were both in diapers.

Talia Hale and Claudia Stilinski had been the best of friends as well as allies, with Claudia using her magic to serve as the Hale Pack Emissary.

However, with Claudia's unfortunate passing (due to her magic a Werewolf bite would have killed her instead of saved her from her disease), the role of Emissary was taken over by Deaton.

And, with Stiles just turning 18 around a month ago, he has now began training under Deaton to take his spot and continue on his mother's legacy.

 

So, with the connection between Talia and Claudia, when they found out they were both pregnant, Talia a few months ahead of Claudia, they vowed to have their children grow up together and be best friends like they were.

 

And, once they were both around 8 and Derek started talking about how good Stiles smelled and Stiles started talking about how he could feel Derek's emotions as if they were his own, the two mothers realized that their sons were mates.

Overjoyed, they explained what mates were as best they could to their young sons.

And, if that promoted Stiles to drag Claudia to the store to buy ring pops because " _I'm gonna marry Derrie Momma, so I gotta per-, prah... pur.."_

_"Do you mean 'propose' sweetheart?"_

_"Yeah! That!"_

Well, there's still pictures of Stiles down on one little knee, brandishing a cherry ring pop at a giggling Derek, framed and hanging on the walls of both the Hale and Stilinski houses.

 

After that, the pair were inseparable, and although neither of them have brought up the mates thing or even confessed their feelings yet, Talia still sat her son down and gave the proper mates talk when he turned 18 and according to the Sheriff he did the same with Stiles.

(And maybe the Sheriff, all of the Hales, and even Scott and Melissa (whom the Sheriff has been dating for a couple years now), have a betting pool on when their sons will get their heads out of their asses).

Either way, Talia and the Sheriff are both happy that their sons are still the best of friends after all these years.

 

Which leads to where Derek is now.

The pair are both seniors in high school, and Derek is a captain or a co-captain of many of the Beacon Hills High's various sports teams.

Including lacrosse.

And, due to Coach Finstock being the literal worst, Derek now has to haul his ass out of bed to go to a 9:30 AM injury fund game against Rockridge High.

 

"Ugh, Stiles, you couldn't have let me just sleep? This game doesn't even count!" Derek grumbles as goes through his drawers, grabbing parts of his uniform and pulling them on.

"What?! No way Der! You're the freaking captain, you need to go and show everyone how it's done and beat those smarmy Rockridge kids!"

Derek huffs, "Yeah, yeah whatever. Wait...is that one of my jerseys?" He asks, pointing to the red and white home game jersey Stiles is wearing, big number 24 on the front.

 

Derek feels as though he should be surprised at the blush that spreads across Stiles's face, but Stiles has been blushing around him so much lately that it really isn't.

"Uh- yeah, yeah it is. Laura gave it to me when I got here, saying I should show my support...or whatever." Stiles stutters.

Derek doesn't know whether to yell at Laura or thank her.

On one hand, he doesn't want Stiles to feel pressured into supporting him just because their best friends. ' _And mates_ ' his brain  supplies.

On the other hand, Derek can't help the pleased blush he gets whenever Stiles wears his clothes, and the thought of Stiles wearing his jersey with his name on the back, basically marking himself as Derek's...well yeah okay Laura gets a pass on this one.

 

Derek doesn't realize he's been zoning out for so long without responding to Stiles until the boy stutters out a "I can...take it off if it bothers you? I mean why would a jock like you want to associate a nerd like me with you? Ha ha yeah..i'll just-" he finishes with a mumble, starting to pull the jersey off, revealing his usual graphic tee underneath.

 

"Wait wait!" Derek shouts out, startling both himself and apparently Stiles with his sudden outbust, Stiles dropping his hands with a small flail, staring up at Derek.

"I uh, mean, keep it on...if you want to of course. I...like that you're wearing it. And cut the crap about thinking I don't want to be associated with you okay? You're my best friend and everyone already knows it, and I've never given a fuck about what people think about that in the 18 years we've been best friends and i'm definitely not going to start now." Derek rambles. He's usually not so vocal, (as Laura and the rest of his family love to constantly point out) but Stiles has always managed to bring out this side of him, especially when he's nervous.

 

"Yeah?" Stiles responds with a small grin and a blush.

Derek nods with a small grin of his own, and then grabs his bag from the corner of his room.

"Let's get this over with." He sighs out, heading downstairs and outside where his family is waiting in their various cars, Stiles following closely behind him.

 

"You riding with Stiles?!" Laura calls out the window of the Camaro.

"More like is Stiles riding hi-!" Derek's brother Max calls out from the backseat, the rest of his innuendo cut off by Cora coming up in the seat behind him and covering his mouth with her hand.

Derek blushes and shoots a glare at Max, before turning to Stiles, taking in his blush as well.

 

Derek looks towards Stiles's Jeep, his mother's admonishing "Maxwell Robert Hale what did we talk about!" and Cora's shouted "Ew! He licked me!" fading away in the background.

 

"So... are you?" Derek asks.

"Am I what?!" Stiles exclaims in disbelief, blush darkening.

Derek is confused by his outburst until he pieces together the last few minutes of conversation and then hastily backtracks, cheeks burning, "No! Shit wait I meant are you taking me in your Jeep I didn't- I-" 

Stiles cuts him off with a giggle, "Derek it's fine, but yeah I was going to take you if you wanted? I figured it'd be better than trying to squish in with your siblings.

"No, yeah that's fine, i'd take your deathtrap over being squished between Cora and Logan any day."

 

Derek smirks at Stiles's indignant "Hey! Don't talk about my baby that way!" 

"Just shut up and drive" Derek says fondly, but regrets it as soon as Stiles looks at him with a devious twinkle in his eye.

"Don't even think about playing that song on repeat again Stiles." Derek warns.

"My car, my choice." Stiles sing-songs, popping in a CD and putting on track number 6.

Derek groans as soon as the beginning notes of "Shut Up and Drive" by Rihanna start blasting.

 

Derek can hear where Laura, Cora, Max, and Logan are all laughing at his anguish from where they're following behind them.

Derek just flips them off in the rearview mirror.

He winces when he hears his mother's "Derek Robert Hale!" coming from the car behind the Camaro

Werewolf hearing. Gotta love it.

 

***

 

Reaching the parking lot, Derek parts ways with his family and Stiles, but not before Stiles leans in for a slightly longer than normal hug and a mumbled "Good luck Der."

"Thanks Stiles." Derek mumbles back, reluctantly pulling away, and heads toward the locker room.

 

"Wow, so gracious of you to finally show up." Jackson snarks with a smirk.

"Shut the fuck up Whittemore." Derek snarks back with an eyeroll.

 

"He was probably too busy giving Stilinski the business!" Isaac exclaims, smirking as the rest of the team laughs.

 

"Definitely, tell me Derek, is Stilinski's ass as tight as it looks?" Danny leers.

"Woah hey man that's practically my brother you're talking about!" Scott exclaims in disgust while the other guys laugh.

Derek, for his part just rolls his eyes and tries to hide his blush in his open locker under the guise of looking for extra strings for his crosse.

 

Derek isn't mad at the guys for their ribbing, per se.

But he is annoyed.

 

Because well...him and Stiles aren't even together. ' _No clue why_.' A voice in his head that sounds a lot like Laura comments.

 

But, even if Derek grew some balls and finally made a move, and him and Stiles actually got together, Derek wouldn't be fucking Stiles up the ass.

He means he could if Stiles really wanted him to, but Derek doubts it would be all that pleasurable for him.

Because Stiles might be a boy from the torso up.

But downwards he's female.

 

Derek and his family, Scott, Lydia, Allison, the Sheriff, and of course Stiles himself know this.

"This" not being that Stiles is transgender.

Stiles was just...born half and half as he always likes to say.

 

Derek's known since he was a child, due to them taking baths together from time to time.

However, Derek didn't realize it was unusual until he was a little older and started learning basic things about sex organs, gender, and the like.

 

He still remembers being taught what transgender was when his older cousin Josh (now Julia), came out to their family.

So, when the younger kids were confused, Talia decided to explain it as best she could for them to understand.

Derek remembers her giving them an abridged explanation so they'd understand as they did range from ages 5-9: " _The person feels as though they weren't born in the right body or with the right parts so they decide to change to make themselves happier"_

Derek remembers thinking about how his best friend Stiles always referred to himself as a boy but he had "girl bits" as his 5 year old self elegantly put, and asked his mother later that night as she tucked him in if Stiles was what his cousin was.

Talia answered him with a curt " _It's...a little different than that sweetie. Stiles is...special. And, since he's so special you need to keep this a secret okay?"_ and kissed him goodnight.

" _Like werewolf kinda secret?" Derek asked sleepily._

_"Exactly." Talia said with a fond smile, and then added on, "And Stiles is pretty sensitive about it okay? So don't mention it around him, you wouldn't want your mate to be upset now would you?"_

_"No!" Derek exclaimed._

_Talia chuckled fondly as her son's eyes flashed gold. Her heart felt full of affection at how protective her son was of Stiles._

_"Okay sweetheart, sleep now." Talia soothed, softly running her fingers through Derek's hair until he drifted off._

 

So, Derek continued on like normal, just accepting that Stiles's differences were just another part of what made him so perfect, what made him Derek's mate.

 

It wasn't until the pair hit puberty that the topic was broached again, this time being explained in  full detail to the two just-turned-teenagers.

It was then that Talia alongside Deaton, explained how Stiles was a mix of female and male. How sparks and other magic users' DNA doesn't necessarily fit the everyday mold.

Apparently sparks and other magic users could be born in a hybrid form, almost something akin to a hermaphrodite. How it was just a part of life.

Talia explains that due to Claudia's magic she produced what is known to be the most powerful of sparks: one with the strength and agility of a male but with the ability to be fertile of a female.

According to Talia and Beastiary records, throughout history this type of spark was usually a mate to a werecreature, most often a werewolf, and served as both Emissary and mate.

 

Stiles, for his part, looked like this was something he'd known for a while, which didn't surprise Derek; it was his anatomy after all.

Derek was surprised to note how Stiles looked at him shyly, with an almost undetectable note of fear in his expression.

When Talia and Deaton left the pair to themselves, heading instead to Talia's office to go over official pack things and the like, Derek invited Stiles up to his room.

There, Derek sat him down and asked what was wrong.

 

"Wrong? Why would anything be wrong?" Stiles stuttered nervously.

"Stiles, c'mon tell me, you know you can tell me anything." Derek soothed, sitting down on his bed next to his mate, taking one of his hands in his, gently rubbing over the knuckles.

"I guess i'm just worried that you'll think i'm weird...or broken or something and not want to be my mate anymore."

Derek could feel himself gaping in incredulity, "Stiles! Didn't you hear my mom and Deaton? You're literally the perfect mate for me. Throughout history your kind of spark has served as the perfect werewolf mate."

"You think so?" Stiles asks shyly.

"Of course I do." Derek responds quietly, pulling the boy in for a tight hug, smiling when his mate returns it.

 

//

 

Derek is snapped out of his reminiscing by someone hitting him in the back with their cross.

He turns around and faces them, glare on his face, which softens and turns into an eyeroll when he sees the perpetrator wasn't douchebag Whittemore like he thought, but Boyd instead.

"Yo captain, you good? You've been over here staring unseeingly into your locker for the past five minutes."

Derek looks around to notice all the team staring at him, some in confusion and some in concern. "Yeah, yeah i'm fine. Let's go kick some Rockridge ass!" Derek exclaims, heading to the doors leading to the field.

"Hell yeah!" The rest of the guys yell back, following Derek.

 

***

 

It's the last minute of the game and if Derek wasn't a werewolf with supernatural healing he would bet any money that he would be a walking bruise by now.

Rockridge is brutal, and Derek swears their coach is pumping them with some mega steroid.

And their bodies aren't the only things that are huge. They're also huge douchebags.

Derek doesn't think he's heard this many "unnecessary roughness" penalties called in his entire four years of playing high school lacrosse.

 

Their captain, some asshole with the jersey number 1 (and seriously who picks number 1 as their jersey number? Oh right, a self-centered asshole) is the biggest douchebag and has definitely been purposely targeting Derek the whole game.

 

They start up again, and instantly he's tackled again by Rockridge's captain.

Derek doesn't even have the fucking ball this time.

 

He feels his eyes flash, and luckily the only people who notice are his family and friends, who Derek can heard worriedly talking to each other.

He's about to up and punch number 1 right in his smug face when he hears Stiles's voice ring clear through the jumbled noise of the crowd, speaking in a normal register because he knows Derek can hear him, "Derek, don't fight him even though I know how badly you want to. You guys are up by 8 points. Punching him will only cause a full on brawl and you guys will have to forfeit. Don't give that douche the satisfaction."

Derek takes a few deep breaths, letting Stiles's voice anchor him, and feels himself calm.

He finds Stiles in the crowd giving him a nod and small grateful smile, and heads back to where the rest of the team is.

 

Derek manages to outrun number 1 and score a goal right as the clock runs out.

He sends flashes him a smug smirk and heads over to where his team rushes him in grateful congratulations.

 

***

 

After showering and gathering his stuff, and listening to Finstock's eccentric congratulatory speech, Derek heads out to the parking lot where his family and friends swarm him in hugs and pats on the back.

His family tell him they'll see him at home later, more than one of them throwing a wink in and gesturing to Stiles, making him blush.

Allison and Lydia part ways for a girls' night, and Erica goes to find Boyd, leaving him and Stiles alone.

 

"You played really good tonight." Stiles says with a grin.

"Thanks, and thanks for anchoring me so I didn't beat the shit out of that douchebag."

Stiles laughs, "No problem."

 

"So, did you wan-" Derek starts, but is cut off by Greenburg coming out of nowhere with a pat on the back and a "Yo! Captain my captain! Jackson's throwing a celebratory banger at his house, you comin'?"

"He's throwing a party at 12 in the afternoon?" Derek asks incredulously, at Greenburg's nod he continues, "Uh, I'm not sure.." Derek trails off, chancing a quick glance at Stiles, noting the poorly hidden dissapointment marring his face.

"Oh okay, well maybe i'll see you there!" Greenburg yells, (a little too loudly Derek notes with a wince), and heads off towards the other end of the parking lot.

 

"You can go, you know. I don't mind."

"What? No, no it's fine c'mon let's go get some celebratory lunch or something." Derek responds back, heading towards the Jeep.

He's stopped by a hand grabbing his wrist.

 

"Seriously Der, it's fine, go celebrate the win, it'll probably be more fun than hanging with lame ol' me." 

Derek raises an eyebrow, grabbing Stiles's hand from his wrist, and in a moment of boldness laces it with his own, "Stiles, c'mon okay? You seriously think i'd rather go get smashed with Jerkson and his buddies than hang with you?"

"Well- I mean...yeah." Stiles mumbles.

 

Derek huffs, Stiles has always been insecure, but lately it's been getting worse for whatever reason.

"Stiles I like hanging with you. Love it actually. I don't need to go to the party, I don't want to go to the party. I can't even get drunk unless there's wolfsbane involved and Lydia won't be there to mix it correctly so that's out. And even if I _could_ getdrunk i'd still want to hang with you okay?"

Stiles gives a small nod and smile, and Derek sighs in relief that it seems like Stiles is finally starting to understand.

 

They get extra pepperoni on their pizza and then hang out at the Hale house until Stiles has to head home to cook dinner for his father who just got off work.

 

***

Derek is blearily opening his locker, still half asleep.

He's immediately alert however when Stiles sidles up next to him, smelling of pain and the copper tinge of blood.

"I want to die." Stiles groans, resting his forehead against Derek's shoulder.

"That bad huh?" Derek asks quietly.

 

He feels Stiles nod against his shoulder, and discreetly places a hand along Stiles's lower abdomen, glad he wore long sleeves today as he watches the black lines of his hand travel up towards the hidden skin of his forearms.

Stiles sighs against him gratefully, "God, I love you."

Derek feels as though he should tense up at the words, but Stiles has been saying it to him and he to him since they were old enough to speak. The only difference is now Derek wishes Stiles meant it the way he means it. 

 

Because even though they know they're mates doesn't mean it has to be romantically. Platonic mates exist. 

Whenever he argues this his whole family, and even Deaton, all look at him as if he's the dumbest person they know but Derek still stands by his point.

Because he doesn't want to force Stiles into a relationship with him just because they're 'meant to be' or whatever. He wants Stiles to want to date him because he actually wants to, not because he feels like they should.

Hence why Derek hasn't brought the mates thing up to Stiles himself since they were 13.

Derek doesn't know whether to feel vindicated or sad that Stiles hasn't meantioned it either.

 

Derek snaps out of his reverie and softly says "Love you too." in response, pulling away to gather his books for the day.

 

***

It'd just before lunch, and instead of heading to where Stiles is sitting at their usual table after he grabs his food, Derek heads for the vending machine, buying a pack of Reese's for Stiles.

He slides the chocolate towards him when he sits down, trying to ignore the way his wolf preens at providing for his mate.

Stiles's gives him a tired and slightly pain-tinged smile in return, "Chocolate makes it all better right?" He asks rhetorically while opening the package.

 

"Pain back?" Derek asks, taking a bite of his sandwich.

"Mhm." Stiles responds around a mouthful of peanut butter and chocolate.

"I'll drain it again after lunch." Derek responds quietly.

"You're the literal best, you know that?" Stiles says gratefully, making Derek blush.

 

***

 

Later that day, once school is over, Derek ends up cuddled up in his bed with Stiles.

Stiles's head is resting on Derek's chest while Derek is slowly rubbing a hand over Stiles's abdomen, draining any and all of his pain away.

Derek feels a fond smile stretch across his face when he looks down and notices that Stiles fell asleep.

 

He looks down at his arm, seeing that the black lines are gone, meaning all of Stiles's pain is gone for now, but continues slowly rubbing the boy's stomach.

 

Derek thinks back to when Stiles had gotten his period for the first time..

 

They were hanging out at the Hale house alone, his siblings out with their own friends and his parents away for the day at a meeting with a neighboring pack.

Derek and Stiles felt like the coolest kids ever to be given the responsibility of staying home in the big Hale house alone.

They both felt like it was about time they were allowed.

After all, Talia or his dad, Devon, checked in on them periodically through text or call, the outer edges of the Hale property were warded and protected against danger, the house was alarmed, and there were security cameras outside that his parents could view the live feed of from their phones, so they had nothing to worry about.

 

Derek and Stiles has just finished making sandwiches when Derek smelled it.

Blood.

Stiles's blood specifically.

 

Derek felt his eyes flash in concern and worry and turned toward where Stiles was standing, chewing a bite of his sandwich.

Derek instantly became confused, because his mate didn't seem to be hurt in any way.

He headed towards him to make sure, and noted how the blood smell was steadily getting stronger.

 

"Stiles, did you accidentally cut yourself with the sandwich knife or something?" Derek asked, taking Stiles hands and turning them every which way.

Huh. No cuts.

"What? No? Derek are you okay? Your eyes are gold dude."

 

"You smell." Derek says, and at Stiles hurt and offended look he hastily tacks on, "Like blood. You smell like blood, Stiles."

"What? Why would I smell like blood? I have no cuts anywhere." Stiles says confused.

Derek decides to take it upon himself to figure out where the source of the blood smell is coming from, and noses around and down Stiles. It's not until he's at Stiles's hip that he realizes.

 

"Uh...maybe you should go to the bathroom." Derek says.

"What? Why?" Stiles responds confused, but heads to the bathroom anyways.

Derek follows him, noting the red stain on the back of Stiles's khakis.

 

Mumbling to himself, Stiles heads into the bathroom, pulls his pants and underwear down, sits on the toilet, and panics.

"Oh wow uh. Huh." He says lamely, looking at where Derek's hovering in the doorway, not looking at him but at the floor instead.

 

"Fuck Derek what do I do?" Stiles asks miserably.

"Why are you asking me? Shouldn't you know?!" Derek exclaims incredulously.

"Don't yell at me!" Stiles whines, and to Derek's horror promptly bursts into tears.

 

At this, Derek mentally says ' _fuck it_ ' it may be slightly weird now that their basically teens to see each other naked, but Stiles _is_ his mate and he needs him.

Heading over to where Stiles is still on the toilet, he hugs him as best he can given their position, "Hey, hey shh Stiles i'm sorry I didn't mean to yell I'm just panicking a little." He tries to soothe.

"How do you think _I_ feel?" Stiles sniffles, pulling away.

"I know, I know."

 

"And the reason I don't know what to do is dad hasn't gotten around to telling me about this yet. Scott's mom was supposed to do it but they keep giving her crazy long night shifts and i've been...afraid to Google it."

Derek sighs and runs a hand down his face, trying to get a hold of himself, "Okay well, how about we call my mom or one of my sisters-" he starts but is cut off by Stiles.

"No! No! Please don't call them Derek please, this is already mortifying enough." Stiles pleads.

 

Panicking at the sight of Stiles starting to tear up again, Derek relents, figuring he's grown up around sisters, and his mom gave him a pretty thorough sex ed lesson on both sexes recently, so he thinks he could handle this on his own. Maybe. Possibly. Hopefully.

"Okay, okay, no calling anyone, got it."

 

Stiles slumps in relief and Derek takes stock of the situation.

"Well first things first, i'm going to go get you a pair of sweats and underwear okay? I'll be right back."

At Stiles's nod he rushes to his room, digging through his drawers until he finds a pair of grey sweats and a pair of black briefs.

 

He goes into the bathroom and places them on the counter.

"Okay, so now...I'm going to try and find you some...stuff for that okay? I'll go look in Laura's bathroom." Derek rushes out.

 

Derek hopes explaining the situation to Laura will keep her from killing him for going in her room, and opens the door, heading in and towards her bathroom.

He opens the cabinet under the sink and lets out a quiet "Yes!", when he catches sight of a box of tampons and a box of pads.

He can't really remember the difference, so he grabs both and heads back to the bathroom Stiles's is in.

 

"Okay so I got these," he starts, showing the boxes to Stiles, "But I don't remember what the difference is..."

He places the box of pads near Stiles's feet and hands him the box of tampons.

Stiles looks over the information on the back and promptly drops the box, grabbing for the pads instead.

 

"Okay so those apparently are supposed to go in me and I am so not sticking anything up in me so looks like this is the better option." He says, looking over the back of the package. There doesn't seem to be directions like there was on the tampon box.

 

Stiles takes one out, and unwraps it, noticing that one side has some type of absorbent material and the other has what looks to be an almost bandaid-like sticker portion.

"Uh..Der? Did Laura get a like faulty reject box or something? Aren't these backwards, like shouldn't it be sticky on the absorbent side so it can...stick to me?" He asks confused.

 

Derek blushes, thinking back to the videos, mentally thanking him mom for being so thorough on showing him the sex ed for both sexes.

Shaking his head, Derek takes the opened pad from Stiles, "No uh, you actually stick this side to your underwear and then when you pull them on the absorbent side will be...under everything so it can catch everything.

"Oh. Huh." Stiles responds back, blushing.

 

He pulls his own soiled underwear and pants off, pulling the briefs up his legs and takes the pad back from Derek.

"So...where in my underwear should I stick it?" Stiles asks.

Derek thinks back to the video, and then remembers that the underwear he gave Stiles is meant for males.

"Well..I think you're supposed to stick it to the...crotch portion of the underwear," Derek starts, watching as Stiles looks down at the briefs and then back up at Derek in confusion.

Derek continues before Stiles can even fully open his mouth, "But since those are meant for guys there really isnt't one? I can go get a pair of pair of Laura's if you want."

 

"Gross Der no way I am not wearing your sister's underwear like some creep." Stiles says in idignation.

"Okay, okay fine. Then just..stick it in the middle portion of the underwear and then stand up to reposition everything." 

 

Stiles nods, and then hesitates looking down, trying to figure out where the middle portion would be.

Derek sighs, wondering how this day turned so strange, and leans down, taking the pad from Stiles.

 

Removing the backing and sticking it on the briefs, Derek dutifully ignores how he's essentially face to face with Stiles's crotch, and stands back up.

"Okay so..stand and make sure everything's right."

 

Stiles stands, pulling the underwear up.

"So, it should be under my...vagina right?" Stiles mumbles blushing.

Derek's face burns with how hard he blushes, but he nods.

 

He turns away and gather's up Stiles's soiled clothes while the boy adjusts everything and pulls the sweats on.

The toliet flushes, and Derek turns back towards Stiles as he heads to the sink and washes his hands.

"I'll go run these through the wash and see if it'll help against the stain okay? I'll see you in the kitchen."

Stiles nods and Derek heads downstairs.

 

Later on, they're somewhat cuddled up on the couch playing Mario Kart when Stiles suddenly groans, clutching his stomach and his scent turns bitter and acrid with the smell of pain.

"What's wrong?!" Derek turns towards him concerned.

 

"I- I think this is cramps. I've heard Lydia talk about them to Allison before." Stiles grunts out.

"Oh, okay." Derek sighs out somewhat relieved, his mate is still in pain but at least he isn't dying. And, he's heard Laura complain about cramps before too. Apparently they were 'satan's suckerpunches to your stomach', according to her.

Derek tells Stiles as such and he gives a pained sort of chuckle with a "sounds about right".

 

"Here, c'mere." Derek says, pulling Stiles closer to him.

He wraps an arm around him and places his hand on Stiles's abdomen, watching as his veins turn black.

Then, the pain hits him. "God Stiles how are you even alive right now?" He groans out in awe at how strong the pain is.

"No clue dude." Stiles sighs out, slumping against him when Derek's veins stop turning black and all the pain has subsided.

 

Then, Derek remembers something else Laura always said when she got to this 'time of the month'.

He heads into the kitchen, waving a hand at Stiles when he whines out a confused sounding "Where're you going?" 

 

Rummaging through the cabinets, Derek groans in frustration when he can't find any chocolate bars.

Then, he remembers his mom's plan to bake chocolate chip cookies later that week, and looks in the pantry.

Grabbing the unopened bag of chocolate chips, Derek mentally crosses his fingers in the hope that his mother will give him a pass for stealing the chocolate, due to the circumstances.

 

He sits down next to Stiles on the couch, and wraps his arm back around him.

"So, I remember Laura saying how chocolate makes this whole thing better, but I couldn't find any chocolate bars. But I found these!" Derek says, showing the bag of chocolate chips to Stiles.

"You are the best mate ever." Stiles says with true conviction, making Derek preen.

 

His parents come home and find them cuddled up asleep on the couch, empty bag of chocolate chips on the ground.

Talia is about to get angry when she smells it.

Then, she can't stop feeling proud of her son for being such a good provider for his mate.

 

Derek is just glad that now him and Stiles have both basically become pros at handling his monthly time.

 

***

No matter where Stiles went it seems the only thing people keep talking about is prom.

Whether it be about dresses, tuxes, limo arrangements, or the worst one of all: dates.

Stiles is sick of it.

And _no Lydia he is not bitter okay_!

 

Just because he's literally been called Derek Hale's mate since childhood by every member of Derek's family and even by Derek himself doesn't mean Derek wants to date him, let alone go to prom with him.

He's heard the stories about platonic mates okay? He knows him being Derek's mate doesn't guarantee anything.

No matter how much he wished it did.

 

You would think that being told you're mates and having pictures of little kid you proposing to little kid Derek would mean something and maybe urge the freaking sourwolf into making a move.

Nope.

And Stiles is too chickenshit to do it himself.

Hell, he still thinks of himself as broken due to the..way he was born.

No matter how supportive Derek's been.

 

And, as he watches yet another person get promposed to, this time Ethan promposing to Danny, he glares.

And of course that's when Derek sits down across from him.

 

"What's wrong?" He asks, taking in Stiles's expression.

God, Stiles hates that adorable concerned expression on Derek's stubbly, beautiful face.

"Nothing." Stiles says, going back to picking at his mac and cheese with his plastic fork.

 

He hears Lydia huff from where she's seated on his left and can practically feel Scott and Allison's eyerolls from his right.

"Stiles is feeling bitter because people keep getting promposed to and he hasn't yet." Lydia states matter-of-factly.

Stiles glares at her in response, making her smirk widen.

 

"Oh. Well yeah." Derek responds back.

' _Great, he sounds uncomfortable thank's Lydia_.' Stiles tries to communicate telepathically.

Unfortunately his already small spell repertoire doesn't extend to mind control yet.

 

Right at that moment Stiles curses his luck when douchedick Jackson plops his Yves Saint Laurent clad ass down into the seat besides Lydia.

"Yo Hale, heard Jennifer asked you to prom, you gonna go with her and hit that?" Jackson smirks.

"God Jackson if you're going to keep being a pig maybe you should go live on a farm." Lydia admonishes.

 

Stiles though, is frozen. Waiting for Derek's response.

He watches as Derek's gaze flicks to his quickly before turning to Jackson, "I told her I wasn't sure whether I was going yet and that I'd get back to her." He says, and Stiles feels a small bit of tension drain out of him, because at least Derek didn't give a definitive yes.

 

"Oh come on Hale seriously? One of the hottest girls in our class and you don't even give her a straight answer? What's wrong with you man." Jackson says in disbelief.

Derek just shrugs in response and goes back to eating his apple with his adorable bunny teeth.

 

Which of course is when Jennifer Blake herself shows up at their table, practically hugging Derek from behind.

"So Derbear, make a decision yet?" Her red-lipstick painted mouth practically purrs.

It's with that that Stiles decides to just leave.

He can't sit there and bear the possibility of hearing Derek tell her yes.

His heart can't take that.

 

He mumbles out some excuse of being sick from the cafeteria food and high tails it out of there.

He considers hiding out in the bathroom but doesn't want to risk someone coming to look for him, so he just heads out the school to the parking lot, jumps in his Jeep, and heads home.

 

He's barely away from the school before he feels the first vibration of an incoming text from his phone in his pocket, followed by the constant vibration of an incoming phone call.

When he finally reaches a red light he's had what's felt like 20 texts and 5 calls so far, and yanks his phone from his pocket, putting it on silent completely and throwing it onto the passenger seat face down.

 

When he finally reaches his house and lays into his bed, his thoughts catch up to him and he realizes that he may have overreacted a little.

Derek didn't give her a definitive answer before, there's no telling whether he'd have given one then either.

But Stiles couldn't help it, not with the way Derek blushed when Jennifer wrapped around him.

Derek only ever blushed around Stiles. And he was not going to sit around while he watched Jennifer Blake replace him.

 

Although who's he kidding? He never was Derek's too begin with.

And, at least Jennifer has the entire female package.

Not half like him.

 

It's that thought that pushes him over the edge, and he feels the tears start falling.

And when they start they won't  stop.

 

***

Derek is seriously about to punch a fucking hole through the wall.

Stiles just left out of nowhere after smelling like hurt.

And he's not answering his phone.

And when Derek went looking for his Jeep in the school parking lot it wasn't there.

 

"Did you find him?" Scott asks, Allison by his side and Lydia close behind.

"No. I don't know what the fuck happened though."

"Are you kidding me? Derek how are you so dumb?" Lydia asks in disbelief.

 

"Me?! How is this my fault?!" Derek exclaims.

"You let your fucking mate sit there while Jennifer Blake put her hands all over you and asked you to be her date to prom, you don't see anything wrong with that?" Lydia yells back.

"Why would Stiles care? He doesn't see me like that?" 

At all of his friends' looks of disbelief and anger, he deflates.

 

"What?" He asks defensively.

"Stiles. Does. See you that way Derek Robert Hale get your ass to the Stilinski house right now before I kick your ass!" Lydia shouts.

"Okay, okay." Derek says placatingly, following her orders because she is scary as hell and maybe she's right.

She isn't set to be valedictorian for nothing after all, right?

 

Hopping in the Camaro, Derek takes a deep breath and steels his resolve, and heads for the Stilinski house.

 

***

Stiles doesn't even realize he cried himself to sleep until he's startled awake by a knock on his window.

At first, he's afraid something or someone's here to get him, and grabs for his magically reinforced baseball bat, before looking in the window and seeing Derek.

 

He sighs, and flicks open the lock, stepping back while Derek climbs in.

 

He sits down in a heap on bed, and Derek unsurprisingly sits beside him.

He moves his hand away when Derek makes a move to grab it, not looking up to catch the hurt expression that flashes across the werewolf's face.

 

"What the hell Stiles? You just left! I was so worried!" 

"Oh welp. Stiles is a-okay, no worries. You can leave now." Stiles mumbles.

He flinches when Derek grabs his hand but doesn't pull it away this time.

 

"Stiles. Seriously, what happened? Is this...everyone thinks this is about the Jennifer thing...but I told them they're being ridiculous."

"Pft yeah, ridiculous." Stiles scoffs.

Derek's eyes widen when they realize Stiles is lying.

 

"Stiles...you know I told her no right?" 

"Yippee." The boy responds sarcastically.

 

Eyebrows furrowed, Derek uses the hand not holding Stiles's own and gently coaxes his head towards him, kaleidoscope eyes meeting sligtly puffy and red rimmed golden amber.

"Stiles? Do you...like me?" Derek asks, ignoring the burning of his cheeks and the anticipatory dread building in the pit of his stomach.

"Why's it matter?" Stiles asks, trying to move his gaze away from Derek, but Derek's grip on his face remains sure yet still gentle.

 

Derek decides he's in deep, might as well go even deeper and says, "Because I want to know whether my feelings are reciprocated. I want to know whether everything's one sided. I want to know if my...mate...loves me as much as I love them."

"Derek..." Stiles whispers in awe.

"Yeah?"

"Do you...mean that? Do you love me?" The spark asks in disbelief.

"Yes, I think I have ever since you proposed to me with a ring pop." Derek states.

 

Suddenly, Stiles face breaks out into the most beautiful smile Derek's ever seen on his mate's face. 

"I love you too." Stiles says back, and Derek's surprised at how different those four words sound from all the other times Stiles has said them.

 

Derek's grinning so hard his cheek muscles twinge, but he still leans in, Stiles meeting him half way.

The kiss itself at first is just a meeting of smiles, because neither of them can stop.

Eventually though, they're able to tone it down enough for their lips to meet.

And Derek doesn't think he's ever felt anything more perfect.

Judging by the small appreciative moan Stiles lets out he feels the same

 

A couple hours later, when their lips are a little too sensative and swollen from all the making out, the pair cuddles up, Stiles laying on Derek's chest, Derek's arms around him.

"Y'know...just because we're dating now doesn't mean a promposal wouldn't be nice." Stiles states with a smirk.

Derek looks down at him fondly, "Okay." He says simply.

 

 

The next day brings with it Derek walking in to the cafeteria with a giant cardboard sign reading "Prom?" on it.

"Prom" is spelled out in ring pops attached via some hot glue.

Stiles says yes. Maybe he tears up a bit. No one can prove it. (Except Scott totally can because he got the entire thing on video and Lydia and the rest of their friends took pictures).

 

***

Stiles runs towards the door when he hears the Camaro's horn signaling Derek's arrival.

"Really son? You two finally become a thing and the boy loses his manners? What happened to coming in and saying hi?" The Sheriff tsks from his perch on his recliner.

Stiles rolls his eyes fondly, "First off daddio, don't even try and sound upset I know you won the betting pool because you chose this month." At the Sheriff's sheepish look he continues, "And Derek hasn't lost his manners, we're just already running behind for this tux fitting appointment. Speaking of, gotta go dad!" Stiles throws over his shoulder, heading out to the car.

 

"Sorry, sorry, dad kept me." Stiles apologizes, climbing in.

"It's fine," Derek sighs, "We're already late anyways, why not be a little later? I hate suit fittings anyways." 

"Well, in that case.." Stiles trails off, pulling Derek in for a short kiss, aware that his father's watching from the living room window.

"Mm" Derek hums pleased, pulling out of the driveway and heading downtown.

 

When they reach "Ted's Tuxes & Steve's Suits", Stiles leans in and asks, "How did you find this place again?" 

"Peter. He apparently comes here all the time. And i've been here before whenever I needed a suit. Henry's pretty good."

"Wait, _Henry_?! What happened to Ted and Steve?" Stiles asks.

Derek laughs and holds the door open for Stiles, the bell over it tinkling, "They don't exist. I guess Henry just liked how it rhymed."

 

Stiles shakes his head with a small laugh and walks up to the front counter where they're greeted by a very old looking man.

"You two catch traffic?" He asks.

"Yeah, there was a lot." Derek lies, raising an eyebrow when Stiles smirks at him.

After all, Henry doesn't need to know that the real reason they're late is because Derek forgot to set his alarm and slept in, only waking when Talia went to check on him, causing him to panic and hurriedly get dressed. Which explains why his shirt's inside out, Stiles notes with a fond grin.

 

"Ah well that's alright, I don't have another appointment for a few hours. Why don't you two browse the suits and tuxes and find which ones you want and then i'll fit you."

The pair nod and look around.

Eventually they agree to match, opting for simple black suits with dark blue ties and vests.

 

They show their choices to Henry, who goes on to fit Derek first.

It isn't until Henry gets to the legs, specifically the inseam aka crotch area that Stiles worries.

He's never been fitted for a suit before so he had no idea how this went. Hell, when he needed a suit for his mother's funeral him and his dad were too distraught to get him properly fitted, luckily Talia just got him one she thought would fit pretty well and like always she was right.

But now, Stiles doesn't know how keen he is on an old guy poking around his junk.

Or, at least where his junk would be.

 

Derek must smell his emotions because he looks at him in concern, but Stiles just waves him off.

It can't be that bad right?

 

Stiles was wrong. It's bad.

Henry gets to the inseam area and Stiles can feel him feeling around trying to get a gauge on things and gulps.

"Huh, well you'd think with a name like Stilinski you'd be packing that Polish sausage but guess not huh?" Henry laughs.

Stiles tries to let out a fake laugh but it comes out more a slight sob and he can see Derek gaping out of the corner of his eye.

 

But, at least Henry thinking he has a small dick is better than Henry finding out he has no dick.

Even though the comment hurts like hell.

 

***

Derek is supremely worried. 

Ever since Henry's completely inappropriate comment about Stiles's the boy himself has been quiet.

And anyone that knows Stiles knows how unsual that is.

 

He tried asking if Stiles was okay afterwards, but Stiles just shook his head and vehemently told him to drop it, so he did.

For now.

 

Pulling up to the Stilinski's Derek doesn't even get a chance to ask if Stiles wants to hang out before the boy is hastily climbing out of the car and running into his house.

Derek tries caling out to him and catching up to him but gets ignored.

 

"Woah woah, what happened?" John asks, stopping Derek as he tried to head upstairs.

"Did you hurt my boy Hale?" John bites out.

Derek gulps in fear even though this has nothing to do with anything he did. But can you blame him? John is scary and owns wolfsbane bullets, having all his anger directed on him in one look is terrifying.

 

"No! No I promise." Derek pleads, and then goes on to tell John of everything that happened.

John sighs, "What the hell, is professionalism not a thing anymore? What if Stiles was actually transgender?" 

"I know sir, I think I might cancel our suit order. I have to see what Stiles wants first though."

"Right, right yeah. Go on up ahead. Sorry to have scared ya kid, but you know how I am with my boy."

Derek nods and gives a small grateful smile, heading upstairs.

 

Stiles's bedroom door isn't closed all the way, but Derek still knocks.

When he gets no response however, he heads in.

Stiles is sprawled out on his bed, pillow covering his face.

 

"Stiles? C'mon" Derek says, trying to coax the pillow off his boyfriend's face.

The boy finally gives in, and Derek's heart aches when he's met with Stiles's tear stained face.

 

"Baby.." he practically whines, sitting down next to Stiles and gathering him in his arms.

He soothes him, rocking him slightly, running one hand through his soft unruly hair and another up and down his back.

 

"I don't know which i'm more upset about, the actual comment or how much i'm letting it get to me." Stiles sniffles a little while later, pulling back.

Derek cups his cheeks, using his thumbs to wipe away the stray tears, "You have every right to be upset Stiles, it was an inappropriate comment and after everything you've been through battling self image insecurities you can be as upset as you can." 

 

Stiles sighs, "I know."

"You know you're perfect right? In every way?" Derek asks, lifting his boyfriend's chin when he tries to duck his gaze down.

"Der..."

"Stiles. I mean it. I have never once not thought you were perfect. It doesn't matter what you're anatomy is like, all I care about it how you are as a whole. I love all of you. Not some of you, not half of you, not a third of you...not one fifth o-"

"Okay, okay, I get it." Stiles laughs.

"Yeah?" Derek asks, when Stiles nods shyly, he asks on, "Good." before leaning in for a kiss.

 

One kiss leads to many kisses and to making out, before they hear a throat being cleared and sheepishly look at where the Sheriff is standing in the doorway.

"Now, you know i've always rooted for you two and i'm happy you're together, and that you're both 18 and have the right to...make love or whatever...but don't do it when i'm home please! Or at least close the damn door boys."

"Sorry dad."

"Sorry Sheriff."

"Now Derek, I know I scared you earlier but it's still John." John smirks at him, closing the door.

 

"What does he mean he 'scared you earlier'?" 

Derek blushes, "I ran in here after you and he thought since you were ignoring me that I was the reason why you were so upset and he gave me the scariest glare I've ever seen." 

"Oh god, he gave you the glare™?! I've only ever seen him use it on criminals! No wonder you were scared."

"Yeah, definitely not something i'd like directed at me again...but it's okay, I get it. He loves you so.." He trails off with a shrug.

 

"You're the cutest, you know that?" Stiles asks, booping Derek on the nose.

Derek playfully bites at his fingers.

"Oh hey, did you want me to cancel our suit orders and go somewhere else?" 

Stiles seems to think about it for a little bit, then shakes his head, "Nah, I mean the whole thing was super shitty and if it wasn't for you i'd probably still be a mess right now... _but_ the suits are super nice _and_ I don't want to risk going somewhere else and something similar happening so let's just keep them."

"Okay." Derek answers with a shrug and a kiss to Stiles's cheek.

 

"Oh and Stiles?"

"Mhm?"

"I love you."

"I love you too, you big sap."

 

***

"Out of all the stores in the mall why are we going into CVS? I thought you guys were done and we were finally going to head to the parking lot??" Stiles whined.

 

He was currently nearing the end of an afternoon-long shopping trip Lydia and Allison dragged him on as soon as they got out of school for the day.

It was something they forced him into once or twice a month, usually claiming that it helped to have a guy's opinions on things. (Though Stiles has always thought that that was just their guise for forcing him to occasionally buy clothing other than tee shirts and plaid).

 

The pair of girls told Stiles they were finished ( _finally),_ and they were all heading to the parking lot when Lydia spotted CVS and turned to Allison with a "Oh! We almost forgot!"

Which is how Stiles found himself being dragged into the store.

 

The girls didn't stop until they got to the display of razors.

Stiles figured they just needed to get themselves new ones, but that thought vanished when they both turned to him with smirks.

 

"So Stiles, you and Derek are finally together and you're going to prom together...you know what couples or dates do on prom night don't you?" Lydia asked.

"...Go to after-parties?" Stiles said confused. He had an inkling to what she was implying but waited her out.

 

"No. Well yes, sometimes I guess." Lydia huffed rolling her eyes.

"Stiles...they have sex." Allison chimed in.

"Oh. Right. Yep that. Okay...so what does any of this have to do with razors?" He asked.

 

Lydia gave him her patented look that always made him feel stupid whenever it was directed at him.

 

"Because well...Stiles, have you ever trimmed anything before?" Lydia asked.

"Trimmed...anything?" Stiles responded sounding even more confused.

"Y'know...landscape the..bush." Allison giggled.

"Landscape the...wha-? Oh! Ohh _that_. Hm yeah no...I never really had a reason to?" He responds, rubbing the back of his neck.

 

"Oh, well then you're lucky you have us!" Lydia smiles, turning towards the display, grabbing something, and handing it to him.

"Now, usually I just get waxed, and so does Allison, but we figured you're probably not ready for that...so this is the next best thing. It's a razor specifically for your...area."

 

"Don't forget this!" Allison says, handing Stiles a can of shaving cream.

"Uh...thanks guys.." Stiles trailed off, looking over the items in his hands.

 

"We don't want you to think you have to do this either Stiles. Derek will probably be fine with anything, but I know a lot of people like it better trimmed down...and until you know for sure a little maintenance couldn't hurt!" Allison rambles, smiling.

"Yeah, and if you don't want to shave at all you don't need to either. It's your body and your choice, we just figured we'd help show you the option." Lydia adds.

 

Stiles nods, "Thanks guys. I think I want to do some...'maintenance', i've been thinking about it for a little bit but...don't know how?" 

 

"Just think of it like shaving your face...lather and then shave in the opposite direction of the hair...stuff like that!" Allison says.

"Oh and don't shave too early before prom especially if you're planning on shaving down completely as then they'll be a chance of things getting stubbly before prom night, even though its only three days away." Lydia adds.

 

"Oh okay, okay..." He nodded, heading for the checkout counter.

***

It was the night before prom and Stiles was currently stood in his bathroom, trying to figure out how to go about shaving.

He decided to start with the shaving cream, lathering up slightly, before going in with the razor.

 

After deciding to go completely bare just to see how it'd look and feel, Stiles set to work.

He couldn't believe the whole ordeal took him over half an hour.

But, when he took stock of himself, gently running his fingers down silky smooth skin, he concluded that the time spent was worth it.

 

That is, until the following morning he woke up to red bumps all over his mound and itchiness.

He texted Lydia and Allison in a panic, both of which responded with a myriad of apologies and emojis, saying how sorry they were that they forgot to explain to him how to prevent shaving irritation.

He responded back saying it was okay, but they definitely needed to give him more detailed instructions for next time.

 

He just hoped Derek didn't mind.

If Derek was even planning on having sex with him.

He hoped so.

 

***

Derek couldn't believe prom was finally here. 

He was on the Hale house lawn, standing in his suit (he had Peter pick them up, not even going for the cautionary final fitting because there was no way he was seeing Henry again or worse making Stiles see Henry again), waiting for Stiles.

 

The rest of their friends were already there: Scott and Allison, Boyd and Erica, Lydia and Ethan, Isaac and Cora, and surprisingly Jackson and Danny (according to Lydia, Aiden turned out to be a douchebag and apparently all it took for Jackson to pull his head out of his ass was not only his jealousy but also seeing his best friend hurt yet again).

Everyone was there, except Stiles.

And, he wasn't answering his phone.

 

The limo was set to come soon and Derek was worried Stiles backed out.

However, when he caught sight of the Sheriff's cruiser he let out a sigh of relief.

 

He watched as John climbed out, and then felt his mouth dry up once Stiles climbed out.

"Damn, looking good Stilinski!" Erica whistled, the rest of the group joining in.

Derek could not agree more.

 

"Derek! I am so sorry I'm late the Jeep decided right now was the perfect time to shit the bed but luckily my dad was coming here anyways to take pictures so I just carpooled with him. Oh! And I dropped my phone when I tried pulling it out of my suit jacket and it crashed into a million pieces on the ground so if you tried calling me which you probably did because you're good like that then sorry!" Stiles rushed out.

"Stiles baby breathe." Derek said with a chuckle, leaving a small kiss on his boyfriend's forehead.

 

"Alright! Now that everyone's here, picture time!" Talia shouted.

All of the parents and all of Derek's siblings (except for Cora who was in the line up) lined up along the Hale house lawn for pictures.

They were just wrapping up when the limo arrived.

 

They all climbed in to the various parents's shouts of "have fun!" and "be safe, make good decisions!"

 

***

 

"Oh wow, this place is fancy." Stiles said in awe, taking in the venue. Apparently their class raised a shit ton of money this year in fundraising thus why they were able to afford a sweet-ass place like this.

It was Beacon Hill's nicest country club, and it overlooked the ocean.

Decorated in reds and golds, and big crystal chandeliers hanging from the ceiling, it was definitely the epitome of luxury. (Or as luxury as a town as small as Beacon Hills could achieve.

 

"Yeah it is." Derek agreed, taking in the place as they waited in line for the check in table.

 

"We should get in the line for pictures before it gets too long." Stiles said once they checked it.

Derek hummed in agreement and they got in moderately long line.

 

As the pair neared the front Stiles swore he could hear a very familiar voice yelling posing instructions at the couples being photographed.

Once they got out onto the patio Stiles realized he was right about the voice.

 

"Why the hell do they have Finstock taking the pictures? Did they spend all the money on the venue or something? And where the hell did he get all this equipment it actually looks professional." Stiles leaned over and whispered in Derek's ear.

Derek watched as Finstock did something on his camera and leaned in towards his boyfriend whispering, "Actually Finstock majored in photography in college or something. I think he owned a photography business for a while too before he started working here." 

 

"You're shitting me." Stiles said in disbelief.

Derek opened his mouth to respond but was cut off by Finstock himself.

 

"Hale and Bilinski, whatta couple! Always was hoping you two were together, it would certainly explain why Bilinski here would always disrupt my damn classes by talking your ear off." 

Derek and Stiles let out slightly uncomfortable laughs and nodded.

 

"Alright so, who's holding who?" Finstock asked while poking around on his camera.

Stiles and Derek looked at each other.

Derek raised an eyebrow and Stiles raised his back with a smirk.

Derek rolled his eyes with a small grin before sidling up behind Stiles, wrapping his arms lightly around his waist.

 

"Okay boys all set?" at their nod Finstock barked out "Okay then smile!" before the pair was blinded with the bright white of the flash.

 

It wasn't until Stiles and Derek were heading back inside to their table when a thought occured to Stiles.

"Hey wait! How is the picture going to be any good if there's a big flare from your..wolf eyes?" He whispered.

Derek just smirked, "May or may not have paid Danny to put a special lens covering on Finstock's camera when he wasn't looking. It's the same kind my family always uses. Blocks out eye flare." 

"Oh wow you're so smart boo." Stiles teased, laughing at Derek's affronted look at the pet name.

"That one is the worst, no way. Nope." Derek says vehemently shaking his head, making Stiles laugh harder.

 

***

"Oh my god this ravioli is like orgasmic, whoever picked the menu for this is my new boyfriend." Stiles moaned out while stuffing another piece of the pasta in his mouth.

He almost choked from the laughter that bubbled up when he felt Derek's low growl from where he was pressed up against him in the seat next to him.

 

"Calm it kujo you know you're the only one for me." Stiles teased fondly.

Derek just rolled his eyes, but Stiles could see past it, not only because he's well-versed in Derek Hale facial expressions but also because the small upturn of his mouth gave the werewolf away.

 

***

After a night full of dancing, laughter, and happiness, and with surprise, surprise Lydia being crowned prom queen and Jackson king (followed by Ethan and Danny willingly giving up their dates for a few minutes so the queen and king could participate in the traditional dance together), Stiles found himself back on the dance floor for one final time.

 

Full of good food and even better dessert, and like he could burst with happiness, Stiles wrapped his arms even tighter around the back of Derek's neck, softly swaying back and forth with him to the last slow song and last song of the night.

 

As Florence Welch's rendition of "Stand by Me" played over the speakers, Stiles stared up at the kaleidoscope eyes of his boyfriend, heart tripping when those eyes met his.

 

"I'm really happy I got to go with you Der. I'm so happy we got to this point."

"Me too. It was a long time coming."

"The longest." Stiles agreed, leaning in for a kiss just as the last notes of the song rang out.

 

***

Luckily for the group (or 'pack' as they'd taken to calling it, which was essentially true since they were all in the know and Scott, Erica, Boyd, Isaac, and Jackson were all his mom's betas, Lydia was a banshee, Danny a mage, and Ethan a member of a pack the Hales were allied with), the limo driver was the nicest guy ever and drove each of them to their respective destinations instead of dropping them all back off at the Hale house.

 

So, Stiles couldn't help the excitement and slight nervousness he felt as him and Derek headed inside the empty Stilinski house.

Earlier that day, Stiles's dad told him he was taking a night shift, and he shudders remembering the wink and smirk his dad through in when he said he wouldn't be back until morning, and to not '"make him a grandfather yet".  

 

The pair make their way upstairs to Stiles room, and he stops once they're over the threshold.

He opens his mouth to say something along the lines of "now what?" but is stopped by Derek gently pushing him against the door and kissing the everloving fuck out of him.

 

Stiles relaxes slightly, because this he's familiar with.

Of course just as that thought filters through his mind Derek grabs his ass and encourages him to jump up and wrap his legs around him, before walking them to the bed and softly laying Stiles down.

 

Stiles surges up into a kiss when Derek lays himself over him, before tensing when Derek starts trailing a hand down his abdomen and one over his thigh.

Because yes they're definitely made out before, but there never really was any grope-worthy touching, not like this.

 

Derek must feel him tense up as he pulls away from the kiss, gaze meeting his.

"You okay?" He asks.

"I'm fine." Stiles rushes out.

"I can tell when you're lying Stiles...you know we don't have to do anything just because it's prom night right? We can just make out." Derek soothes.

 

"I know Der I know. But I want to. I'm just really nervous." 

"Well if you want to then okay." Derek says leaning back down.

 

They kiss for a bit more before Derek takes his clothes off in a flourish, leaving him naked.

Stiles feels his eyes widen when he chances a glance at Derek's cock. Because the thing is massive.

 

Stiles apprehensions are moved to the backburner however when the kissing starts back up.

He lets out a gasp when he feels Derek start feeling him through his pants and pulls back, "I should probably take my clothes off too huh?" 

"Yeah, it'd probably be easier that way." Derek says with a smirk.

 

Stiles takes a deep breath and starts taking his clothes off, deciding to treat it like ripping a bandaid off and taking them all off quickly, leaving him stark naked beneath Derek.

 

He can feel his insecurities bubbling up the longer he lays there while Derek just silently stares.

"So.." He says lamely, gasping when Derek meets his gaze, golden glowing eyes on display.

"You're perfect baby." Derek says quietly, leaning down to kiss him again.

 

Derek leans back again and runs his hands down him, including softly trailing his fingertips over his mound.

"What're these bumps?" Derek asks quietly, eyebrows furrowed.

 

Stiles groans and covers his face with his hands in embarrassment.

"I shaved for the first time and apparently there's this whole process you have to go through to prevent irritation that Lydia and Allison forgot to tell me about..."

"Oh, huh. Why'd you shave?" Derek asks, gently taking his hands off his face, holding them in his own.

 

"I didn't know if you'd like hair...I know a lot of guys usually don't so.." He trails off, turning his head into his pillow so he doesn't have to meet his boyfriend's gaze.

Derek gently coaxes his head back, face an expression of affection, "Baby, you didn't have to do that. You would've been perfect no matter what." He says earnestly.

Stiles blushes, "Yeah?" he asks.

"Yeah." Derek says with a smile, leaning in for a kiss.

"Good, because shaving was a bitch." Stiles mumbles against his boyfriend's lips, making him laugh into the kiss.

 

 

Stiles is sliding his tongue along Derek's when he feels him gently grab his hand where it's been resting on Derek's abs, and lead it towards his hard cock, placing it there. 

Stiles's eyebrows go up, startled, but he continues on nonetheless.

It's not like it's a bad feeling.

Actually, he finds he quite enjoys the feeling of a hard cock in his hand, how warm and soft Derek is, and plays a little with the foreskin before Derek halts his ministrations with his own hand.

 

Derek pulls away and traces his lips with his pointer finger and asks, "Want to...try sucking it? It's okay if you don't want to." 

Stiles feels himself freeze, considering it. 

He knows Derek knows he's a a virgin through and through and he knows Derek's one too, so it's not like Derek has high expectations.

Stiles decides that yeah, he wants to try. He's certainly thought about it before, what it would be like.

 

Stiles nods, and Derek gently guides him down towards his cock with a soft hand cupping his cheek.

Stiles decides to just go for it, and wraps his mouth around the tip, sinking down.

 

"Mm no." Derek grunts out, urging Stiles off.

"No?" Stiles asks feeling distraught.

"No no, not like that baby, you're perfect...just don't use teeth." 

"How do I do that?" He whines out, feeling lost.

"I don't know...i've never blown anyone or been blown before...but I think in porn they wrap their lips over their teeth." 

 

Stiles tries to mimic what he's seen in porn too, and manages to cover his teeth with his lips, before going back in.

This time, Derek starts moaning at Stiles's actions, but he finds his gag reflex acting up from how thick Derek's is and how much his mouth is stretched.

 

A particularly harsh gag rips through him, and he pulls off.

"You okay?" Derek asks, running a hand over his back.

Stiles nods, mumbling out "gag reflex." before going back in.

 

However, he finds now matter how shallow he goes he still gags, and pulls off when an even harsher gag rips through him.

"Fuck Derek I don't think I can do it...my stupid gag reflex keeps acting up, sorry."

"That's okay baby, we can do other things. C'mere." Derek says, pulling Stiles up for a kiss.

 

 

They're been making out for a little while when Derek starts mentioning looking for a condom.

Stiles's stomach knots up at the mention because he knows he's nowhere near "ready".

He's well versed in self love okay? He knows he's not turned on enough, not wet enough.

 

Derek hasn't done much to help, just playing with his nipples and sucking and biting his neck and collar bones while occasionally touching him.

He even mumbled something earlier about Derek maybe eating him out but either Derek didn't hear him or ignored it altogether, and he didn't want to repeat himself like a jackass.

 

He decides to just go with it and hope for the best.

"Ready?" Derek whispers in his ear as he gently spreads Stiles's legs.

Stiles just nods in response, feeling Derek lining himself up at his entrance.

 

He winces as Derek pushes in, eyes slamming shut in pain.

"You okay?" Derek asks, sounding concerned.

"Hm yeah just hurts." Stiles breathes out.

"Oh yeah. Well, it's supposed to hurt the first time right? I'll be gentle." 

Stiles nods and breathes out a shuddering breath as Derek starts to move.

 

He thinks this is probably some of the worst pain he's felt.

It burns like hell and feels like he's being split open.

"Der baby, play with my nipples and suck my neck or something." Stiles bites out.

"Yeah, like this?" Derek asks, doing as Stiles says.

Stiles nods, but the actions don't distract him enough from the pain as he had hoped.

 

A little while has passed when Derek starts thrusting harder and deeper and Stiles feels tears slowly leaking from the corners of his eyes.

"Maybe- may- _ah-,_ could you go back to the shallower thrusts please?" He practically whines out.

Derek complies and the pain dies down a little.

But don't be mistaken, it still hurts like hell.

 

A little later on Derek mumbles something from where he's buried in Stiles's neck.

"What?" Stiles asks.

"Nevermind." Derek says.

 

"What? No that wasn't a bad 'what' it was a 'what I can't hear you' kind."

"Oh...I asked if I could cum on you." 

 

Despite the pain and thinking about how him and Derek are definitely going to have to have a captial D level Discussion later on making sure Stiles is fully turned on, Stiles can't help but marvel at how cute his boyfriend is with his blush.

"Wolf thing?" He asks.

Derek just nods in response.

"Yeah, yeah go ahead." He answers.

 

Moments later Derek pulls out and Stiles can't even take in the relief he feels at the fact, before he's feeling warm wetness drip onto him.

He looks up in time to catch Derek finishing up with stripping his cock, before he collapses down beside him, slowly rubbing his fingers through his mess.

 

Eventually the cum turns tacky and Derek gets up to get a washcloth to clean it off.

While his boyfriend heads to the bathroom, Stiles decides to sit up and take stock of things.

 

It isn't until he sits up fully that he notices the smear of red under him, and slowly reaches down with shaky hands to touch his sore core, fingers coming away red.

It's that moment that Derek walks in, and Stiles sees his eyes flare gold and widen in panic.

 

"Did you- did you get your period?" Derek stutters.

Stiles shakes his head, feeling miserable.

"So I...I was the one- fuck! I can't I can't shit fuck fuck!" Derek whines out.

 

Stiles moves to grab for his boyfriend in an effort to calm him down, but Derek's too fast.

Stiles sits in shock as Derek opens his bedroom window, full-shifts into his wolf, and jumps out, running away.

 

Feeling numb, confused, and pissed off somehow all at once, Stiles decides to go to bed, not even caring if his sheets get even more bloodstained.

 

***

 

Stiles wakes up to the sound of his front door closing.

He listens as his father's familiar sounding footsteps ascend the stairs before stopping outside his room.

 

His door opens and he sits up, meeting his father's suprised gaze.

"Hey, thought you'd be fast asleep right now kiddo, where's Derek."

"He...left." Stiles says, hoping his father won't detect the hurt in his tone.

Unfortunately for him, his dad's not the Sheriff for nothing.

 

"What do you mean 'left'?" John asks, complete with air quotes.

"Things went...weird and Derek freaked out a little, or a lot I guess, shifted fully and kinda jumped out of the window and ran?"

 

"Son, you gotta give me a little more detail here before I go and shoot the Hale kid." John sighs out, pinching the bridge of his nose before sitting down at the foot of Stiles's bed.

"He..it wasn't good. The whole.. _thing._ He made me bleed and then freaked out about it...Please don't make me fully say it dad, use your Sheriff skills." Stiles pleads.

 

"Bleed...oh! Oh...kid huh. Well that wasn't entirely his fault son, you would've bled at least a little either way. I know your mom did and things definitely weren't..bad."

"Yeah but I think because he's my mate and he hurt me he freaked. I probably smelled like a lot of pain too so.."

"Ah hell kid, you know better about this than I do, I wasn't there thank god. Go talk to the kid, it's early but not too early. And if he's as distraut as you're making it seem then he probably didn't sleep anyways." John says, pulling Stiles in for a hug.

 

"Thanks dad, love you."

"Love you too, now i'm gonna go to sleep, goodnight."

"Night dad."

 

***

As soon as Stiles walked up to the front door of the Hale house, it was swung open by a concerned looking Talia.

"Stiles! Thank heavens you're here! Maybe you can tell me why my som refuses to shift back. Or at least go and talk to him to try and get him to shift back." 

"Yeah, sure, is he up in his room?" He asks, heading inside.

At Talia's nod Stiles heads upstairs.

 

He doesn't bother knocking, knowing Derek already knows it's him.

The big black wolf on the bed raises its head from beneath its paws, flashes its golden eyes at him, and whines.

 

Shutting the door, Stiles heads over to the bed, laying down on the space Derek makes beside him.

"There is no way i'm having this conversation with you when you're in this form Derek, so shift your ass back." Stiles sighs out.

 

He watches as the wolf besides him suddenly turns into his naked boyfriend, and sits up once Derek sits back down after pulling some sweats and a tee shirt on.

 

"You left. Why?" Stiles asks deciding to get right into it.

Derek sighs, looking at him with a contrite expression, "I hurt you Stiles, and I was too caught up to realize until it was too late. And I panicked and then my wolf panicked too and so I left..i'm so sorry."

 

"Dammit Der c'mere." Stiles sighs out, pulling his boyfriend towards him until he's plastered against his side.

"I was planning on talking things over once it was all done but you left before I could." 

 

"Talk what things over?" Derek asks sounding nervous.

"Talk about how you didn't do really much of anything to turn me on. To make me...wet. And how when I asked you to do something you ignored me."

"What did you ask me to do?"

"I asked if you'd eat me out and you just ignored me babe."

"What? When? I'm so sorry baby I definitely would have, I was actually thinking about it but was worried it was too far. My wolf was going crazy the whole time about finally claiming my mate so my attention was in and out."

 

"Well see? This all could've been talked about last night." 

"I know...i'm sorry. Are you still hurt? I can't believe I hurt you. It was just the wolf thing and then having no reference on how to go about things properly being a virgin too and i'm sorry."

"You don't have to keep apologizing Derek, it's okay. I can tell you didn't intentionally hurt me and I forgive you. As for the hurting, i'm still sore, but the bleeding stopped."

 

Stiles watches as his boyfriend's eyes flash gold at the mention of the blood.

"I still can't believe I made you bleed, I made my mate bleed." Derek whines miserably, eyes glassy from unshed tears.

"Shh, Der, it's okay.", at his boyfriend's vehement shaking of his head he continues, "No matter how you did things I still would have bled because you'd be breaking through my hymen. Most people bleed at least a little, unless their hymen was already broken or they were born without one. Would there have been less blood if things went differently? Maybe because things probably would've been more relaxed and the glide would've been easier, but there still would've been blood."

 

"Yeah?" Derek sniffles.

"Yeah." Stiles nods, wiping away the tears from Derek's face before pulling him in for a hug. 

 

"We're having a complete do-over though, just so you know." Stiles mumbles into Derek's shoulder.

He feels him laugh lightly. 

"Okay, as many do overs as you want. And then..." He trails off.

 

"And then what babe?" Stiles prompts, pulling out of the embrace.

"And then maybe you could...take my virginity..." Derek says blushing.

"Your...but I thought I did already?" Stiles asks confused.

 

"Well yeah but...not that." Derek mumbles.

When Stiles just looks at him lost, Derek grabs his boyfriend's hands before placing them on his ass.

He blushes deeper when he sees the look of recognition on Stiles face.

 

"Oh! Okay but...how?" 

"I've uh...seen porn where a girl will use a...strapon. I've even seen ones where there's a strapon that has a vibrator for her on one end and then the..dildo on the other. And I looked it up online and they do exist outside of porn so..."

 

Stiles eyebrows shoot up followed by a pleased smirk stretching his mouth, "You've been researching this huh?" He asks.

"Shut up." Derek says sounding embarrassed, turning his gaze to the sheets below him.

 

"Hey hey, none of that okay?" Stiles says softly, cupping Derek's cheek and guiding his head back up to face him again.

"That idea sounds so hot I think i'm sweating okay? Don't ever be embarrassed to tell me something you'd like to try."

"Okay, but that goes for you too." Derek relents.

"Deal." Stiles smiles, leaning in for a kiss.

 

"How about you go get your laptop and show me some of this stuff while we cuddle?" Stiles suggests.

"Sounds good." Derek responds, standing to grab his laptop.

 

Just as he's sitting back down, gettinf situated and cuddled up with Stiles, a knock sounds on his door.

Sighing, he stands to let his mother in.

 

"So, everything okay now? None of us can hear anything when the door's closed because of the soundproofing." 

"Yes mom, everything's okay." He answers, turning to look at Stiles with a fond smile.

 

"Okay good, i'll check in with you boys later!." Talia says, turning around and closing the door behind her.

 

When Derek sits down once again, Stiles cuddles up to him, laying his head down on his chest.

"Stiles?"

"Yeah?"

"I love you." 

"I love you too."

 

***

It's the last couple of weeks of senior year and you can tell the teachers have given up just as much as the students have.

Finstock literally has just been playing movies and all other teachers have essentially given them free periods.

Needless to say, getting up and going to school isn't such a pain in the ass when you know you're not going to have to do any work really.

Except, Stiles is kind of dreading going today since its the mondah after prom weekend, and he's going to have to face a prying Lydia and Allison who are going to want to know all the details about prom night.

 

Speaking of.

"Stilinski, details, now." Lydia says as she slides up next to where he was at his locker, Allison right behind her.

 

"It was fine, good." Stiles says and winces knowing Lydia'll see right through him.

"Stiles, it offends me that you even think that was a passable lie." She says rolling her eyes.

He sighs, "Fine, fine. It wasn't great...things got messy and communication didn't happen too well. _But_ we talked it out and figured things out for next time. That's all you're getting from me okay?" 

 "Ugh fine. So you guys are good then?"

"Yeah, definitely."

 

"Well that's good, glad you guys figured it out." Allison chimes in with a smile.

"Yeah, what she said Stiles. Now i've gotta go find Ethan, plus your boyfriend just walked in so...see you in class."

"Bye Stiles!" Allison says, heading off to find Scott, Lydia going in the opposite direction to find Ethan.

 

Stiles turns to his left just as Derek gets to his locker.

"Hey." He says, leaning in to leave a kiss on Stiles's forehead.

"Hey." He responds back with a smile.

 

"They grill you a lot?" Derek asks gesturing vaguely to where Lydia and Allison just were.

"Eh not too much, they backed off when I gave the summarized version."

"Oh okay." 

 

"Ready to go watch another movie with Finstock?" Stiles asks excitedly, smile growing when Derek takes his hand in his own.

"Definitely." Derek answers, smiling at the blip he heard in Stiles's heartbeat when he grabbed his hand.

 

***

 They don't try and have sex again for around a week.

It's the weekend after prom, and they're once again at the empty Stilinski house, the Sheriff working another night shift.

 

Stiles lets out a quiet hum of satisfaction as Derek's body blankets his, his boyfriend's teeth marking up the side of his neck.

"We should be doing this with less clothes on." Stiles pants out, sitting up to start ridding himself of his clothes when be feels Derek nod in agreement against his neck.

Derek's hands halt his progress however, making Stiles look up at him, confused.

 

"Let me. I want to take this slower than last time. Okay?" Derek says, running his thumbs softly over the knuckles of Stiles's hands.

"Okay." Stiles nods.

Derek gives him a soft smile before slowly sliding Stiles's plaid shirt off of his shoulders.

 

He gently encourages Stiles to lay back down with a hand to his chest, before blanketing him again.

He rucks up his mate's shirt slowly, kissing each new area of skin exposed, until the garment is a rolled up mess in Stiles's armpits, making the boy giggle.

Derek smiles at the sound before moving back enough for Stiles to sit up slightly, helping him pull the shirt over his head.

 

Back against the mattress once more, Derek leans over his boyfriend and places a gentle kiss to his sternum, before trailing a line of kisses to his left nipple, taking the nub into his mouth.

He can feel himself harden even more at the sounds his ministrations drag out of Stiles, and kisses over to the other nipple, repeating his actions, sucking and biting gently while his hand rolls the other one in his palm.

 

Once the nubs are equally peaked and red, he trails light kisses down Stiles's lightly defined stomach, stopping to kiss the moles that intersperse the path to his light happy trail.

Once there he licks down the soft almost peach-fuzz esque line, before laying kisses on Stiles through his pants.

 

He pulls back and lifts his head to meet Stiles's gaze, raising an eyebrow and thumbing over the button of his jeans in silent question.

With a nod and a blush from his boyfriend, Derek pops the botton before slowly pulling the pants down, Stiles lifting up to get them over his butt.

Pulling the pants down and off, Derek kisses his way back up to Stiles's center, smiling along the way as kisses to certain areas or small nips bring forth small giggles and snorts from his boyfriend who apparently has ticklish legs.

 

Back to where he started, Derek trails his fingers lightly around the bottom edges of Stiles's boxers.

"I don't think i've ever seen you so quiet." Derek teases.

"Shut up." Stiles says with an eyeroll, "It's just a lot to take in."

"A good a lot or a bad a lot?" Derek asked worriedly.

"Good, definitely." His boyfriend answers, expression full of affection.

 

Derek is just about to ask if he can remove Stiles's last article of clothing but is cut off by his boyfriend himself.

"Y'know i'm feeling a little unequal here in nakedness...I think it's your turn." He says sitting up, putting his hands up under Derek's henley.

 

Derek chuckles before helping Stiles push his shirt off, gasping lightly when he rubs him through his pants before unbuttoning them.

Standing up off the bed to take them fully, he decides to go for broke and slides his underwear down too, preening slightly when Stiles's smell of arousal intensifies.

 

Laying back over his boyfriend, he raises an eyebrow while playing with the elastic on his boxers, pulling them off when Stiles nods.

He runs his fingers gently down Stiles's skin, noting the short hairs that have grown back, feeling soft under his fingertips.

 

Leaning over Stiles he meets him for a heated kiss, mumbling a "Just as beautiful as ever." against his lips.

Feeling the answering smile, he kisses his way back down Stiles's body, stopping to lave over his nipples again, until he reaches Stiles's core.

 

He hovers over the skin, breathing out a "This okay?" meeting Stiles's eyes.

"Yeah, yes more than." His boyfriend breathes out, making him smile.

 

From there he leans in slowly before placing a soft kiss on Stiles's pubic bone before trailing kisses along his outer labia.

Running a finger along his folds, Derek gently spreads him, before leaning in to kiss his inner ones.

 

Thinking back to the porn he's watched and the articles he may have researched....once after the whole prom night fiasco, Derek moves his mouth up to the top inner part, licking over the small bump there.

"Fuck Derek do that again." Stiles moans out above him, and Derek does.

Laving over the nub, Derek continues running his fingers over the folds, trying not to preen when he feels them turn slicker, wetter.

 

He softly moves two fingers towards Stiles's entrance, and is about to pull away to ask if that's an okay thing for him to do, but Stiles beats him to it by whimpering out a "Please, please Derek god need you. Just be gentle okay?" 

Derek nods before gently pushing his fingers in, feeling his cock drip at the loud moan Stiles lets out.

 

Going back to licking over Stiles's clit, he starts moving his fingers in and out slowly, and crooks them up, feeling Stiles get even more wet as he lets out a near explosive moan above him.

He continues moving his fingers, occasionally crooking up and making Stiles whimper, the slick sounds of Stiles's wetness sounding so loud in the quietness of the room.

 

A few moments later he feels Stiles's throb before whining out a "Don't stop!" and then suddenly he's clenching around Derek's fingers, a fresh wave of slick leaking out over them and his tongue.

 

He pulls away and licks his fingers clean before wiping his mouth, and leans over his still panting boyfriend for a kiss.

Pulling away, Derek runs his fingers through Stiles's slightly sweaty hair, gazing at him lovingly.

"You're so beautiful when you cum baby. And you taste so good." He says, delighting in the blush and shy expression that spreads over Stiles's face.

"Yeah?" Stiles says with a small smile.

"Definitely." He mumbles against his lips, leaning in for another kiss.

 

"Still want you to try fucking me again." Stiles says quietly, pulling away.

Its those words that remind Derek of his almost painfully hard cock, and he nods, reaching for the nightstand where the box of condoms sit. As well as a small bottle of condom-safe lube that Derek picked up after his..research (he basically spent the night after his and Stiles's prom night conversation Googling how to properly have sex and make it good for your partner).

 

He's about to rip into the small foil packet when Stiles's hand closes around his wrist, "Can I?" He asks.

Derek nods, handing him the condom, watching how he opens it and then gently rolls it on, moaning at the light feeling of fingers on his cock.

He grabs the lube and slicks himself up a little, before kneeling  before Stiles.

 

"So, how do you want to do this? I was thinking maybe you could ride me because then you could set the pace?" Derek suggests.

"Yeah, yeah that sounds good." Stiles nods, sitting up.

 

Derek turns over and sits up against the pillows leaning against the headboard, running his fingers down Stiles's sides as he straddles him.

Stiles grabs his dick and positions it at his entrance, before slowly starting to sink down.

Derek stares at him lovingly, and Stiles stares back just as lovingly, before leaning in for a kiss.

 

Slowly, Stiles starts to bounce up and down slightly, gently working Derek in, before moaning when he finally bottoms out.

"Fuck." Stiles breaths out, hiding his face in Derek's neck, peppering kisses there.

"You okay?" Derek asks, running a hand down his back, cupping an asscheek and giving a slight squeeze before going back up.

 

"Yeah, 'm just really full. You're so big Der." He mumbles.

Derek feels his wolf preen and rolls his eyes at it.

"Mm well you're taking me so well baby, so tight around me."

 

Stiles pulls back and meets him for a heated kiss, before moving up and down in a slow but steady rhythm.

Derek moans at the feeling, Stiles echoing him with a moan of his own.

 

They've got a steady rhythm going, one that's slowly growing faster when Stiles pants out, "Der I- I can't my legs are burning I-"

Derek cuts him off by smoothly rolling them over until Stiles is beneath him and he's hovering above.

 

"Fuck that was hot. I think I have a manhandling kink." Stiles moans out.

Derek gives him a smug grin which earns him a fond glare that quickly turns to eyes screwed shut in pleasure when Derek starts thrusting again.

 

Derek can feel his control slipping, and feels his eyes flash.

He tries in vain to get them back under control but finds he can't.

He can't find it in him to worry too much when Stiles's opens his eyes and promptly moans when he sees his eyes.

 

In addition to his control slipping, Derek can also feel the warmth of an approaching orgasm building in his lower abdomen.

"Are you- are you close? Do you think you could come from this?" Derek pants out.

"I, I think so. It feels like it." Stiles pants back.

 

"Should I speed up, go harder?" Derek asks.

"A little bit of both, and maybe play with my clit?" Stiles suggests. 

 

Derek complies and soon he can feel Stiles clenching around him, his own thoughts drowned out by Stiles loud moans of pleasure.

The vice-like grip of tightness around his cock is enough to push him over the edge and he moans, emptying himself into the condom.

 

Catching his breath, he pulls out, leaving a kiss on Stiles's forehead when he winces slightly at the feeling, before taking off and disposing of the condom in the trash bin besides Stiles's bed.

 

Laying down besides his boyfriend, he smiles when he cuddles up to him, laying his slightly sweaty head on his chest.

 

"So...better than last time?" Derek prompts when a few minutes pass with Stiles still not saying anything.

"Way better Derek. A million bajillion times better." Stiles moans out.

 

"Yeah?" Derek asks, trying to reign in the smug smile that's trying to make a home on his face.

"Yeah." Stiles responds, looking up at him, pursing his lips for a kiss.

Derek chuckles and complies, meeting his boyfriend's soft lips with his own.

 

"I love you." Stiles sighs out.

"I love you too."

 

"...I really need a shower I feel so sweaty right now." Stiles blurts a few minutes later.

Derek, who was drifting off into a nice doze, just opens one eye and mumbles out an "okay."

Stiles rolls his eyes fondly, "I was hoping you'd maybe join me?"

 

Instantly, Derek is alert, and Stiles laughs.

"C'mon wolfy, let's go get cleaned up." Stiles says, grabbing Derek's hand in his and pulling him towards the bathroom.

 

Derek feels his heart swell at the nickname.

Stiles gave it to him when they were still toddlers after he saw Derek shift for the first time, and now only uses it whenever he's feeling particularly affectionate.

"Okay Sti." Derek says trying to sound put-upon, smiling when he hears Stiles's heart trip in his chest at Derek using his own rarely used toddler-thought up nickname.

 

He's surprised at how well he remembers when it happened, given that the pair of them were only four.

 

_"Stiles baby, Derek has something exciting he wants to show you!" Claudia calls, smiling when her little son toddles over from the pile of rocks he was looking at._

_Derek looks at him shyly from his position behind Claudia, his Momma over to the side looking proud._

 

 _Looking back at his Momma and_ _seeing her nod, he quickly takes off his clothes before letting the shift take over him._

 _He hears Stiles gasp and looks up just as the little boy goes over and wraps his arms around him_.

" _Wolfy!" He yells in excitement, running his hands through Derek's fur._

 

_Derek and his wolf feel good for making his mate happy, and for his mate accepting him._

_He pounces on Stiles gently, knocking him into the soft grass before licking his face._

_Stiles squeals in joy, and Derek tries to stay shifted as long as he can, but feels himself shifting back._

_Momma says that he'll be better at controllin' it when he's older, and Derek hopes she's right_.

 

_"Woah! You're not furry no more!" Stiles yells with a pout._

_"Sorry." Derek says, feeling sadness overcome him at disappointing his mate._

_"It okay, lov' you n-ways." Stiles says hugging him, not seeming to care that Derek's naked_.

 

_He's about to say he loves Stiles too when suddenly he's being tickled along his sides._

_"Noo! Stiles, stop! Sti- Sti- no!" He_ _pants out around giggles._

_Stiles stops, "What'd you just call me?" He asks._

_"Oh I called you 'Sti'. I woulda called you Stiles but couldn't breathe from you ticklin' me!" He says, sticking his tongue out._

_"It's okay, I like Sti!" Stiles says sounding excited._

 

" _If you get ta be called 'Sti' what do I get to be called?" Derek pouts while taking his clothes back from his Momma, pulling them back on._

_"You get ta be Wolfy of course!" Stiles exclaims with a grin._

_"Oh. Okay." Derek agrees happily_.

 

Derek is snapped back from his memories by Stiles waving his hand in front of his face.

"You comin'? The water's gonna get cold." He asks before climbing in to the already running shower.

"Yeah." Derek says fondly, climbing in behind him and closing the curtain.

 

***

" _It came in_." was all the text from Stiles read, but it still made Derek's heart speed up in excitement.

The excitement quickly drained when he thought of the worst case scenario and quickly texted back " _Your dad wasn't there when it did was he_?" 

 

" _No, no thank god, he was in bed, he got in at like 5 this morning from last night's shift and the delivery guy came right as I was eating breakfast_." Stiles responded back.

 

Derek breathed out a sigh of relief, " _You hid it right_?" he sent back.

 

" _No Der I went and put it on my dad's bed for him to see. What do_ you _think_?" He got back moments later.

 

Rolling his eyes at his boyfriend's sarcasm, Derek sent back a middle finger emoji and a " _See you at school._ " to which he got back a middle finger emoji followed by around 20 different hearts.

 

Grinning, he sent back a heart and then headed outside to where Cora was waiting in the passenger seat of the Camaro.

"You know you might have only a few days left of classes but I still have two weeks and would like to not spent those in detention for being late." Cora snarked.

Derek rolled his eyes with a mumbled "yeah, yeah." before hopping in and heading to the school.

 

***

 "I can't believe your dad is pulling another shift after working a night shift." Derek says as him and Stiles enter the empty Stilinski house.

"Yeah I know. I think he's trying to get extra money in for my grad gift. I think it might be tickets to a Met's game because I heard him talking over the phone with Melissa about it."

"More like you were eavesdropping, don't act like you just happened to hear it." Derek teases.

"Sometimes, I don't like how well you know me." Stiles says sheepishly back.

 

Derek snorts, following his boyfriend upstairs to his room.

He playfully swats Stiles on the ass earning him a glare and a pretty blush.

Derek just raises an eyebrow and smirks.

 

He lays down on the bed while he watches Stiles reach up and grab a box from the top shelf of his closet.

He sits down besides him and Derek sits up, peering into the open box.

Stiles takes the item in question out and Derek blushes, feeling his cock twitch.

 

It's white in color, and one end has a thick looking, good length dildo while the other has a moderately sized dick shaped vibrator that points upwards instead of out.

Stiles takes out black strips of elastic fabric, which must be the strapon element of the whole thing.

 

Derek takes the items from him while Stiles rummages through the box.

"Hey look! They included picture instructions!" Stiles says, brandishing a piece of paper with pictures of a man and a woman on it, each one numbered with a small description beneath it.

"Gotta say though, this girl definitely has better boobs than me." Stiles laughs.

 

Derek snorts, taking the piece of paper from him and blushes while reading it over.

"So...did you want to try this today or another time? Because I mean i'm down for today, its definitely a good distraction against all this graduation stress." Stiles rambles.

 

Derek nods absently, thinking everything over.

Because Stiles is right, graduation stress has run rampant.

Somehow the school decided Finstock was the perfect person to lead graduation rehearsal, and if Derek has to hear him yell at Greenburg one more time about how to properly shake hands while grabbing the diploma Derek'll tear his own hair out.

 

Derek's just grateful that that's really the only stress associated with graduation.

He means, he definitely is sad when he thinks about the pack spreading out to different colleges but that's what's skype is for.

Afterall, him and Stiles both chose  to go to Berkeley even before they finally started dating, Stiles majoring in criminology and Derek in history. 

They've even requested each other as roommates so Derek is pretty content.

As long as he has Stiles with him he can handle any and everything.

 

He's snapped from his thoughts by Stiles's "Hey, you in there somewhere?"

Derek shakes his head to clear it and looks up, "Yeah, yeah was just thinking. But yeah let's try it now."

"Okay yess uh, I guess you should lay back?" Stiles says, straddling Derek when he complies and lays back.

 

Stiles leans over his boyfriend, meeting his lips in a sweet kiss, before trailing down his neck, nipping at his jawline.

Sucking a hickey into Derek's neck, Stiles watches with a pout as it slowly heals, but continues on, kissing down Derek's collarbone, laving over the protrusions with his tongue.

 

It isn't until he's trailing his hands underneath Derek's henley that he realizes he started absentmindedly grinding down onto the bulge in Derek's pants.

He finds he likes the feeling of Derek's hardness rubbing along his pussy, happy that the last week laziness caught up to them and they both opted to wear sweatpants that day.

One particularly hard grind against Derek rubs him along Stiles's clit through his pants and he lets out a quiet moan, one Derek returns.

 

He urges Derek to take his shirt off by rucking it up, and Derek takes the hint, sitting up and peeling his henley off before sliding his sweats off too.

Stiles follows suit by shucking off his own clothes, leaving him in just his boxer briefs.

 

He takes a moment to drink in the beauty that is his boyfriend.

Between the shirt smattering of chest hair, to the abs, to V of his hips, to his dick, Stiles doesn't know where to look the most.

He settles on his dick, leaning down and tentatively mouthing at it through the fabric of Derek's underwear, mouthing more insistently when Derek moans out at his actions.

 

Fabric wet with a mix of saliva and precum, and Derek a moaning mess, Stiles decides now's as good a time as ever and tugs Derek's boxers down.

Derek helps him by leaning up so the boxers can go down over his ass, and Stiles quickly finishes pulling them all the way off.

With a blush, he takes off his own underwear before leaning over Derek who surges up for a less than chaste kiss.

 

Stiles is tugging Derek's bottom lip between his teeth when he feels one of his boyfriend's hands gently rubbing over his folds, the thumb circling his clit.

He moans out and pulls away.

"You know this is about you this time right?" He says with a raised eyebrow.

Derek raises his own eyebrow and responds "Its about you just as much as me baby."

"Yeah well, still. Maybe we should start getting into it..? You should turn over." He blurts.

 

"If you wanted to see my ass all you had to do was ask." Derek teases with a smirk, turning over onto his stomach.

Stiles rolls his eyes and smirks, "Why would I want to see your ass so badly when so much of it is already present in your personality?" 

Derek snorts in response, playfully swatting Stiles's own ass as he bends over to get the lube on the nightstand.

 

Stiles gasps at the feeling before moaning.

"Huh, gonna save that information for later." Derek says from where his head is turned on the pillow, always expressive eyebrows raised in surprise.

Stiles blushes, mumbling out a "Shut up." before going back to stradding the back of Derek's thighs.

"Never said it was a bad thing baby, it's actually really hot." Derek says placatingly.

 

"Yeah, yeah." Stiles tries to aay bitingly, but his small pleased smile gives him away.

Then he goes quiet as he takes stock of the situation, not quite knowing where to start.

He thinks back to porn he's watched, and decides he wants to try something. If Derek's okay with it that is.

 

"Der? Can I try rimming you?" He asks.

Derek lets out a moan in response following by a vehement head nod, and Stiles grins before bending down.

He takes in the beauty that is Derek Hale's back and the work of art that is his ass and sighs, wondering how he got so lucky.

 

He decides to start by kissing down said muscled back, and starts by laying a gentle kiss to the back of his boyfriend's neck, before kissing, nipping, and licking his way down.

Reaching Derek's ass, he pulls back slightly before taking a cheek in each hand and squeezing appreciatively.

 

"The like 1% body fat you have is definitely all in your ass babe." Stiles says, kneading the globes lovingly.

Derek looks at him over his shoulder and rolls his eyes, but his red ears and small smile give him away.

Stiles smiles back before taking a deep breath and deciding to go for it.

 

Leaning down, he spreads Derek open gently, before lightly licking down his crack all the way to his balls.

Emboldened by Derek's noises, Stiles goes in and licks a hard line over his hole, sucking on the dusty rose rim before leaving a wet kiss.

He continues his minstrations until Derek begs out, "Please Stiles I need more please."

"Shh shh, i've got you babe." Stiles soothes, sounding more confident than he feels.

 

He grabs for the lube, slicking up his fingers, before taking his index finger and slowly circling his boyfriend's rim, feeling the furled skin against his fingertip.

He keeps circling, afraid to get to insertion too soon, before Derek lets out a literal short growl followed by a whine, "Stiles, baby I won't break I promise. And...I do this to myself sometimes...or a lot. So don't worry."

Stiles moans out at the mental image of Derek fingering himself open while he gets off, and nods before slowly pushing in his first finger.

 

Derek moans appreciatively and Stiles starts moving the digit, before adding a second.

With two fingers in, he starts scissoring his boyfriend open, feeling along his hot inner walls, before crooking them, thinking back to anatomy class diagrams.

He knows he's found what he's looking for when his middle finger brushes over a slight bump and Derek sobs out a moan.

 

Feeling his muscles giving way to his fingers even more, Stiles adds a third, before going back to licking and sucking at Derek's rim.

 

He's worked up to a forth when Derek's steady stream of moans once again turn into a plea, "Stiles, i'm ready, so so ready, please c'mon."

"Okay, okay, shh, i've got you." He says quietly, and gently pulls his fingers out, running a hand down his boyfriend's back when he whines at the loss.

 

He takes the dildo strap system from where it's been resting by his hip, along with the directions paper.

He's putting everything together when he hears Derek whine.

"I know, sorry baby. I should've done this before I got you all ready." Stiles apologizes.

 

Derek just nods in response, and watches him as he slides on the black straps that are essentially a jock strap, except the cup area has a hole for the rest of the dildo to go through.

Meeting his boyfriend's gold to green flickering eyes, he takes the dildo, remembering one side is supposed to go in him.

He's wet, but not too wet, and he's kind of afraid to try and put anything in when he's not fully ready, not too keen on getting a repeat performance of prom night.

He supposes he could use lube but still figures his inner walls aren't exactly open enough so lube wouldn't do much. 

 

"Uh..dammit. Why are we so bad at this crap?" He sighs

"What's wrong?" Derek asks, sounding concerned.

"I just remembered this is supposed to go in me...and I'm not exactly 'ready'." He responds sheepishly.

"Oh, well that's an easy fix, c'mere." Derek says simply, rolling over onto his back.

 

"Uh, okay, where should I go..?" Stiles trails off.

Derek gestures to his face and Stiles's eyes widen in realization, while his cheeks burn in arousal.

 

Knee-walking up the bed to besides Derek's head, Stiles straddles Derek's face, holding himself above him.

"This is a view I could definitely get used to." Derek says smugly.

Stiles just hits him lightly on the shoulder in fond admonishment, making his boyfriend chuckle beneath him before gently grabbing Stiles by the hips and lowering him to his mouth.

 

He's about to make a snarky comment about hurrying up, but anything he was about to say was cut off by a gasp at Derek laving his tongue over him.

He moans as Derek laves over his clit, feeling his short, soft, beard-like stubble rub over his folds.

 

It's a surprisingly short while later when he feels the familiar building sensation in his belly, and the pleasurable tingling in his insides, slowly spreading to his entire pussy.

He's slowly grinding down onto Derek's face now, and he would feel embarrassed if he couldn't literally feel his boyfriend's moans.

All it takes is Derek dipping a finger in him for him to moan out a "Fuck, Derek!" and coming.

 

This time though, he feels a sensation he hasn't felt since the time he decided to experiment and see how many times he could make himself come in a day.

It almost feels like peeing, but pleasurable, and he pulls back off of Derek, in apprehension.

 

His fears are proven when he kneels to the side of Derek and looks at his face.

His face that is shiny with not just slick, but squirt.

 

"Der- i'm so sorry I didn't mean to i'll go get you a facecloth or somethi-" he starts but is cut off by Derek blurting

"Fuck, Stiles you need to get in me now before I come and ruin this whole thing."

"You're not..turned off?" He asks confused.

 

Derek wipes his face before licking his fingers, making Stiles throb.

"Does it look like I am?" Derek states, gesturing to his golden glowing eyes and rock hard cock.

"Well, I-. No." He responds lamely.

"Stiles, that was literally the hottest thing ever. I reisgned myself to that being one of those things that only happened in porn. I can't believe how lucky I am, fuck you have no idea." 

Stiles blushes, pleased at Derek's earnest sounding words, and nods.

 

He moves back and gestures for Derek to turn over again, before taking the dildo in hand again.

Pulling down the front part of the jock strap, he gently coaxes the upward vibrator inside him, switching it on.

He moans at the feeling before slipping the other end through the opening of the jock, pulling everything up.

 

Kneeling up behind his boyfriend who is now positioned on hands and knees, presenting his beautiful ass and still open hole to him, he lubes his fingers up again before testing if Derek is ready again, making him whine.

 

He slicks up the dildo, feeling the vibrations along his hand.

"Hey babe, you know this is going to vibrate in you too right?" He asks, just making sure.

"Yeah." Derek breathes out.

 

"Okay...ready?" He asks, blanketing himself over his boyfriend's back, wrapping his hands around his waist, dildo poking at his entrance.

"Ready." Derek moans out, so Stiles starts pushing in.

 

Stopping whenever he feels Derek tense up, Stiles finally bottoms out, the pair moaning in unison.

"You can move." Derek says, and Stiles does.

 

Starting a slow easy rhythm of thrusts, Stiles moans at Derek's sounds coupled with the feeling of the vibrations in his own hole.

Thinking back once again to porn he angles his hips up, grinning when Derek's moan goes high pitched, knowing he's hit his prostate.

 

Thrusting, he revels in the power he feels.

He never thought he'd ever get to experience this.

 The idea of using strapons would have never occured to him if Derek never suggested it.

But, as he feels Derek tense and moan out a "So close, you close baby?" he can't help feeling glad that it did.

 

He is, in fact very close to being pushes over into orgasm, and says as such, picking his thrusts up and taking a hand from Derek's waist to rub his clit.

"Can you touch me? Please baby." Derek moans out.

"Of course, anything for you Der." Stiles says with a kiss to Derek's back, taking his other hand from Derek's hip and wrapping it around his cock.

 

Starting to stroke him, Derek moans again, this time turning his neck to the side, "Mark me Stiles, please. Make me yours." 

Stiles feels himself throb at the action, knowing what it means. Knowing that it is the highest form of trust and love you can get from a were.

 

Leaning down he sinks his blunt human teeth into Derek's neck, thrusts faltering in rhythm as he comes, Derek following him, covering his hand in warm cum.

 

Stiles pulls back, laving over the bite with his tongue before kissing it lovingly.

Pulling away, he pulls out, quickly ridding himself of the vibrator as the sensations become too much for his over sensitive insides.

 

Shimmying out of the jockstrap, he cuddles up to Derek, who's turned over onto his back.

 

"That was amazing." Derek pants out, cupping his cheek and gazing at him lovingly.

"Yeah, definitely." Stiles agrees, leaning in to press his slightly sweaty forehead to Derek's.

 

"Maybe we should just skip school and graduation and just stay here and have really amazing sex forever." Derek mumbles sleepily.

"Sounds like a plan." Stiles mumbles back.

 

Derek pulls back and places a soft kiss to his forehead, mumbling a quiet, "I love you." into his skin.

"I love you too." Stiles smiles.

 

"...you set the alarm clock right? My mom'll kill me if i'm late for dinner." 

"Yep, it's all set." Stiles yawns.

 

"You're the best." Derek responds sleepily.

 

***

Caps thrown and caught in celebration, and congratulatory hugs from friends and relatives received, Stiles practically runs over to his boyfriend, pulling him in for a tight hug.

 

"Can't believe I bagged the salutatorian." Derek whispers in his ear.

"Oh please." Stiles says with an eyeroll and a shy smile.

"I liked when you thanked me in your speech. I love you." Derek says with a grin, pulling him in for a kiss.

 

Stiles mumbles an "I love you too." against his lips, when suddenly he feels something hit him in his leg.

He pulls away and looks down at where a light purple dahlia is resting against the side of his and Derek's feet.

Derek reaches down and grabs it, and Stiles looks over at where a girl from their class's bouquet fell apart and is blowing away in the wind.

 

"Huh. Out of all those flowers to blow over here it's my mom's favorite kind." Stiles says in amusement.

"Probably her way of telling you she's with us." Derek says softly with a gentle smile.

 

He pulls Stiles in for a hug when he notices his smile turning watery, mumbling a "She'd be so proud of you, she _is_ so proud of you."

"She's proud of you too." Stiles mumbles back, making Derek give a shaky smile of his own.

 

***

Around 5 years later at their wedding out in the preserve, Stiles notices a patch of light purple dahlias right behind the makeshift altar.

He points it out to Derek later on, noting how they usually don't grow somewhere like the Preserve and the pair share a soft smile.

 

***

Three years later they have a daughter.

They name her Dahlia Claudia.

 

 

 

**Author's Note:**

> Alternate titles for this fic could have been:  
> • The In-Depth Boypussy Stiles fic No One Asked For
> 
> • Stiles and Derek Are Bad At Sex at First (Like Any Normal Human Beings Seriously Everyone Stop Writing First Time Fics Where Stiles/Derek Are Magically Sex Gods)
> 
> • Stereksale7's Excuse to Write a Fluffy Boypussy Fic
> 
> • Stereksale7's Excuse to  
> Sterek-fy How She Lost her Virginity in an Effort to Cope with How God Awful It Was
> 
> Take your pick ya'll
> 
> Either way, I tried to write this in a way that turned the whole boypussy thing more serious (or as serious as something like this can get), instead of treating it like a full-on kink.
> 
> When I originally was thinking of this plot, I thought of writing full-on female Stiles but liked the element of insecurity and body dysmorphia that came along with the whole package.
> 
> Also didn't want to write actually trans Stiles because I didn't want to risk treating such a serious subject badly in any way.
> 
> That being said, hope you all enjoy!
> 
> And as always, comments, kudos, and bookmarks are the wind beneath my wings <3
> 
> XxKait


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